How to fire someone

Back in 1991, I was working at a startup that provided ambulance dispatches. I was the IT/product manager guy, keeping the software running and letting the developers know how it could be improved.

Then, one of our offices shut down and I took over managing the call center.

Suddenly, in my mid-20s, I was managing 50 people, some of whom had been doing the job for longer than I’d been alive. It was very intimidating. While it felt like trial by fire, bit by bit I improved. Twenty-five years later, I think I’ve figured out how to be a leader and not a boss.

And while I pride myself on being good at having direct conversations, one of the most difficult parts of my job will always be making the decision to fire someone.

Over the years, I’ve hired and fired hundreds of people and dealt with all kinds of situations. But after a lot of trial and error, I’ve come to the following conclusion: The best way to approach firing someone is to put your company hat on when you’re making the decision and replace it with your human hat when you deliver the news.

So, what does that mean?

Wear the company hat

Most of the companies I work with and mentor in my role at Techstars are small — they’re made up of hungry, passionate people who dedicate much of their lives to achieving a common goal. Part of that means early mornings, late nights, frequent travel in search of funding or customers and often sharing a lot more about our personal lives than may be the norm at corporations with thousands of employees.

In other words, the people we work with are also people we consider to be our friends. So, it’s no surprise that making the decision to fire someone can sometimes feel impossible as you consider all of the personal factors that come with firing someone: He’s really nice; it will devastate her; he has a family to support; we spend time together socially.

But as a leader, you have to force yourself to avoid the temptation to prioritize personal factors when it’s just not good for the long-term health of the organization to keep that ineffective person around.

That’s why it helps to put the company hat on. Although it’s hard, try to be dispassionate about the person and consider factors such as work performance, effect of the person on overall morale and even what kind of precedent allowing an unproductive team member to stick around sets within your organization.

Put the human hat back on

Once you’ve made the decision to let someone go, it’s time to put the human hat back on. First and foremost, be sensitive. While this is a business decision for you, getting fired is a monumental event for the person on the other side of the table and can have serious repercussions.

Be direct and concise, let him or her know that you have bad news and try to briefly explain why the firing is happening. Then be quiet and let the person react. This last part is important; in our nervousness, we tend to babble on to fill the awkward silence. You’ve had time to think about how to deal with this conversation but, for some people, this is unexpected, and it may take more time to process the news.

Remember that each person reacts differently, so it’s best to let each person react in his or her own way. Some will want to talk you out of it, some will get mad and just want to leave, others will be sad and want to talk about how it will affect them personally.

Try to be sensitive and don’t offer blame, raise your voice or get into an argument. Listen and respond accordingly for a reasonable amount of time, giving the person the opportunity to voice feelings and feel heard.

Have an exit strategy

That being said, always be sure to think through your exit strategy ahead of time, in the event the conversation drags on and you need to bring it to a close. You can try, “Well, you can pick up your final paycheck on Tuesday.” Find something that lets the person know the conversation is over and the decision is final.

Let me reiterate that firing someone is never easy — in fact, it is so difficult that some people avoid it entirely. But the most important advice I can give to anyone about firing someone is to follow through. There is nothing worse you can do for your organization than to continue to let a poorly performing team member linger, perpetuating the cycle of either bad behavior or poor performance, and signaling to the rest of your organization that it’s acceptable.

Letting someone go can be unpredictable, potentially volatile and incredibly stressful, and there are no guarantees that it will end on a positive note without any negative consequences.

But as the leader of your organization, or a manager within it, it’s your responsibility to make the decisions that will put the team and organization in the best position to succeed.

Remember the two hats you need to wear at times, and you’ll put yourself in a position to do just that.